The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
88(1), С. 371 - 383
Опубликована: Дек. 23, 2022
A
cooperative
tertiary
amine/palladium-catalyzed
sequential
reaction
process,
proceeding
via
a
[4
+
3]
cyclization
of
isatin-derived
Morita-Baylis-Hillman
Expansion
(MBH)
carbonates
and
tert-butyl
2-(hydroxymethyl)allyl
followed
by
[1,3]-rearrangement,
has
been
found
developed.
range
structurally
diverse
spiro[methylene
cyclopentane-1,3′-oxindolines]
bearing
two
adjacent
β,γ-acyl
quaternary
carbon
stereocenters,
which
are
difficult
to
obtain
conventional
strategies,
were
obtained
in
good
yields.
Further
synthetic
utility
this
protocol
is
highlighted
its
excellent
regio-
stereocontrol
as
well
the
large-scale
synthesis
functional
transformations
compounds.
Moreover,
control
experiments
probably
established
plausible
mechanism
for
cyclization/[1,3]-rearrangement
process.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(24), С. 4412 - 4439
Опубликована: Ноя. 16, 2023
Abstract
Spirooxindoles
are
privileged
scaffolds
in
diverse
bioactive
natural
products
and
pharmaceuticals,
significant
achievements
for
the
construction
of
these
molecules
have
thus
been
made
past
years.
Among
them,
organocatalysis,
particular,
nucleophilic
Lewis
base
catalysis,
has
recently
emerged
as
an
efficient
reliable
method
preparation
valuable
functionalized
spirooxindoles.
According
to
different
kinds
catalysts,
we
summarize
classify
three
catalytic
strategies;
tertiary
amine‐catalyzed
cycloadditions,
NHC‐catalyzed
phosphine‐catalyzed
respectively.
Through
methods,
potential
spirooxindole
skeletons
owning
various
functional
groups
can
be
produced
enrich
small
organic
molecule
library.
In
this
review,
describe
a
comprehensive
updated
advances
cycloaddition
reactions
Meanwhile,
related
mechanism
application
annulation
strategies
product
total
synthesis
will
highlighted
detail.
Chemical Communications,
Год журнала:
2024,
Номер
60(27), С. 3717 - 3720
Опубликована: Янв. 1, 2024
The
substrate-enabled
switching
of
the
regioselectivity
allows
for
efficient
regiocontrol
via
[4+1]
and
[3+2]
annulations
ninhydrin-derived
MBH
carbonates
with
α,β-unsaturated
ketones
to
access
highly
substituted
furans
cyclopentene.
Chinese Journal of Organic Chemistry,
Год журнала:
2022,
Номер
42(10), С. 3051 - 3051
Опубликована: Янв. 1, 2022
Chiral
heterocyclic
compounds
are
an
important
class
of
chiral
substances,
which
widespread
in
many
drugs,
pesticides
and
catalysts.Therefore,
the
efficient
asymmetric
synthesis
these
becomes
a
research
hotspot
organic
synthesis.Transition
metal-catalyzed
cyclization
with
heteroatom-dipole
precursors
is
method
to
construct
frameworks.Among
them,
designed
based
on
transition
allyl
or
propargyl
substitutions
have
been
extensively
studied
past
two
decades
occupied
role
this
field.The
cyclizations
introduced
detail.The
advantages
existing
problems
current
methods
analyzed,
would
provide
useful
reference
for
researchers
related
fields.
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
41(21), С. 2825 - 2831
Опубликована: Июнь 25, 2023
Comprehensive
Summary
We
developed
a
novel
Pd‐catalyzed
[4
+
4]
cycloaddition
of
(benzo)furan‐derived
azadienes
with
homo‐TMM
all‐carbon
1,4‐dipoles
in
situ
generated
from
α
‐allyl
malonate
derivatives,
affording
an
array
benzofuro[3,2‐
b
]azocines
and
furo[3,2‐
good
to
excellent
yields
(up
96%)
exclusive
regioselectivities.
This
methodology
featured
mild
reaction
conditions
functional
group
tolerance.
The
synthetic
utility
was
demonstrated
by
gram‐scale
reaction.
Furthermore,
the
catalytic
asymmetric
version
has
also
been
explored.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(11), С. 2648 - 2652
Опубликована: Янв. 1, 2023
Herein,
we
disclose
the
first
Pd-catalyzed
enantioselective
(4
+
3)
cycloaddition
of
N
-2,2,2-trifluoroethylisatin
ketimines
with
2-methylidenetrimethylene
carbonate.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 11, 2025
A
Lewis
base-catalyzed
[4
+
3]
annulation
between
dinucleophilic
indole-2-carboxamides
and
Morita-Baylis-Hillmann
(MBH)
carbonates
was
developed
to
access
densely
substituted
indole-1,2-fused
diazepanones.
This
reaction
is
initiated
by
a
N-allylic
alkylation
of
the
indole
scaffold
with
MBH
carbonates,
followed
intramolecular
Michael
cyclization.
Notably,
selectivity
this
process
controlled
removable
o-methoxyphenyl
(OMP)
directing
group
attached
indole-2-carboxamides.
The
wide
scope
substrates,
high
regio-
stereoselectivity,
diverse
transformations
highlight
potential
synthetic
utility
method
in
drug
discovery.
Organic Letters,
Год журнала:
2021,
Номер
24(1), С. 100 - 104
Опубликована: Дек. 10, 2021
A
cascade
assembly
between
isatin-derived
Morita–Baylis–Hillman
carbonates
and
o-hydroxybenzylideneacetones
has
been
developed
under
the
relay
catalysis
of
Pd(PPh3)4
DBU,
affording
a
spectrum
1,2,3,4-tetrahydrodibenzo[b,d]furan
architectures
incorporating
spirooxindole
motif
in
moderate
to
good
yields
with
excellent
diastereoselectivity.
The
fused
indole
analogues
were
similarly
furnished
by
employing
benzylideneacetones
having
an
o-TsNH
group.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(21), С. 4521 - 4527
Опубликована: Авг. 7, 2024
Abstract
Catalyst‐controlled
switchable
(4+3)
and
(4+2)
annulation
reactions
of
Morita–Baylis–Hillman
carbonates
with
benzofuran‐derived
azadienes
have
been
established.
Employing
PCy
3
as
the
catalyst,
reaction
could
provide
a
variety
synthetically
useful
benzofuro[3,2‐
b
]azepines
in
good
yields
(80–92%)
excellent
chemo‐
regioselectivities
via
cycloaddition
reactions.
Whereas
changing
catalyst
from
to
DMAP,
were
switched
construct
highly
substituted
spirotetrahydroquinoline
scaffolds
three
sequential
stereocenters
containing
all‐carbon
spiro‐quaternary
efficiency
diastereoselectivities
(92–96%
all
cases>25:1
dr
)
annulations.
In
addition,
synthetic
utility
this
method
was
further
showcased
by
gram‐scale
transformations
product.
Angewandte Chemie,
Год журнала:
2022,
Номер
134(31)
Опубликована: Май 27, 2022
Abstract
We
herein
demonstrated
an
efficient
method
for
the
atroposelective
construction
of
nine‐membered
carbonate‐bridged
biaryls
through
vinylidene
ortho
‐quinone
methide
(VQM)
intermediates.
Diverse
products
with
desirable
pharmacological
features
were
synthesized
in
satisfying
yields
and
good
to
excellent
enantioselectivities.
In
subsequent
bioassays,
several
agents
showed
considerable
antiproliferative
activity
via
mitochondrial‐related
apoptosis
mechanism.
Further
transformations
produced
more
structural
diversity
may
inspire
new
ideas
developing
functional
molecules.
